JPS6126529B2 - - Google Patents
Info
- Publication number
- JPS6126529B2 JPS6126529B2 JP51122993A JP12299376A JPS6126529B2 JP S6126529 B2 JPS6126529 B2 JP S6126529B2 JP 51122993 A JP51122993 A JP 51122993A JP 12299376 A JP12299376 A JP 12299376A JP S6126529 B2 JPS6126529 B2 JP S6126529B2
- Authority
- JP
- Japan
- Prior art keywords
- benzene
- trifluoromethyl
- bis
- trichloromethyl
- chloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 27
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 24
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 16
- -1 chromium halides Chemical class 0.000 claims description 10
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 239000008096 xylene Substances 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 229910052801 chlorine Chemical group 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- 229910052731 fluorine Chemical group 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052787 antimony Inorganic materials 0.000 claims description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 claims description 2
- 239000001103 potassium chloride Substances 0.000 claims description 2
- 235000011164 potassium chloride Nutrition 0.000 claims description 2
- 239000011698 potassium fluoride Substances 0.000 claims description 2
- 235000003270 potassium fluoride Nutrition 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 239000011775 sodium fluoride Substances 0.000 claims description 2
- 235000013024 sodium fluoride Nutrition 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000011135 tin Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 238000009835 boiling Methods 0.000 description 15
- GGZIUXGYCNYNNV-UHFFFAOYSA-N 1,3-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC(C(Cl)(Cl)Cl)=C1 GGZIUXGYCNYNNV-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- SJBBXFLOLUTGCW-UHFFFAOYSA-N 1,3-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C(F)(F)F)=C1 SJBBXFLOLUTGCW-UHFFFAOYSA-N 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- SKWWCKGHUDPXOZ-UHFFFAOYSA-N 1-(trichloromethyl)-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C(Cl)(Cl)Cl)=C1 SKWWCKGHUDPXOZ-UHFFFAOYSA-N 0.000 description 8
- VDEUYVGUNSJXAE-UHFFFAOYSA-N 1-(trichloromethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1C(Cl)(Cl)Cl VDEUYVGUNSJXAE-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XXZOEDQFGXTEAD-UHFFFAOYSA-N 1,2-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1C(F)(F)F XXZOEDQFGXTEAD-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
- AXVLZOYLQOEKAO-UHFFFAOYSA-N 1,1,2,2,2-pentachloroethylbenzene Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)C1=CC=CC=C1 AXVLZOYLQOEKAO-UHFFFAOYSA-N 0.000 description 2
- XYKZEZPREAUXDQ-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethylbenzene Chemical class FC(F)(F)C(F)(F)C1=CC=CC=C1 XYKZEZPREAUXDQ-UHFFFAOYSA-N 0.000 description 2
- WEWXCIOGPKAVFO-UHFFFAOYSA-N 1,2-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1C(Cl)(Cl)Cl WEWXCIOGPKAVFO-UHFFFAOYSA-N 0.000 description 2
- NTFZDVDWIVFEEI-UHFFFAOYSA-N 1-(trichloromethyl)-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(C(Cl)(Cl)Cl)C=C1 NTFZDVDWIVFEEI-UHFFFAOYSA-N 0.000 description 2
- OUYZWORNIIOVQI-UHFFFAOYSA-N 1-chloro-2-fluoro-3-(trichloromethyl)benzene Chemical compound FC1=C(Cl)C=CC=C1C(Cl)(Cl)Cl OUYZWORNIIOVQI-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 150000004820 halides Chemical group 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
- DDTHLQVVHGZPQB-UHFFFAOYSA-N 1,3,5-tris(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC(C(Cl)(Cl)Cl)=CC(C(Cl)(Cl)Cl)=C1 DDTHLQVVHGZPQB-UHFFFAOYSA-N 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- PDCBZHHORLHNCZ-UHFFFAOYSA-N 1,4-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(C(F)(F)F)C=C1 PDCBZHHORLHNCZ-UHFFFAOYSA-N 0.000 description 1
- RMXLFMXXVKFMFK-UHFFFAOYSA-N 1,4-dichloro-2,5-bis(trichloromethyl)benzene Chemical compound ClC1=CC(C(Cl)(Cl)Cl)=C(Cl)C=C1C(Cl)(Cl)Cl RMXLFMXXVKFMFK-UHFFFAOYSA-N 0.000 description 1
- RFKQAUHDXUCURX-UHFFFAOYSA-N 1,4-dichloro-2-(trichloromethyl)-5-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Cl)=C(C(Cl)(Cl)Cl)C=C1Cl RFKQAUHDXUCURX-UHFFFAOYSA-N 0.000 description 1
- UXMNSLMVCBBGCW-UHFFFAOYSA-N 1-(dichloromethyl)-2-(trichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=CC=C1C(Cl)(Cl)Cl UXMNSLMVCBBGCW-UHFFFAOYSA-N 0.000 description 1
- JIJFXGFHPXLJME-UHFFFAOYSA-N 1-(dichloromethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1C(Cl)Cl JIJFXGFHPXLJME-UHFFFAOYSA-N 0.000 description 1
- LYADDKODNUCIMF-UHFFFAOYSA-N 1-(difluoromethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)C1=CC=CC=C1C(F)(F)F LYADDKODNUCIMF-UHFFFAOYSA-N 0.000 description 1
- ZLOJNFNSRBFZJT-UHFFFAOYSA-N 1-(trichloromethyl)-3,5-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(Cl)(Cl)Cl)=C1 ZLOJNFNSRBFZJT-UHFFFAOYSA-N 0.000 description 1
- OGKCWNMIXCBFQB-UHFFFAOYSA-N 1-chloro-2,4-bis(trichloromethyl)benzene Chemical compound ClC1=CC=C(C(Cl)(Cl)Cl)C=C1C(Cl)(Cl)Cl OGKCWNMIXCBFQB-UHFFFAOYSA-N 0.000 description 1
- XIVDTLKMHDHQCB-UHFFFAOYSA-N 1-chloro-2,4-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Cl)C(C(F)(F)F)=C1 XIVDTLKMHDHQCB-UHFFFAOYSA-N 0.000 description 1
- OMUIIDZYGQSZMN-UHFFFAOYSA-N 1-chloro-4-(trichloromethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(C(Cl)(Cl)Cl)=CC=C1Cl OMUIIDZYGQSZMN-UHFFFAOYSA-N 0.000 description 1
- GMUWJDVVXLBMEZ-UHFFFAOYSA-N 1-nitro-3,5-bis(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 GMUWJDVVXLBMEZ-UHFFFAOYSA-N 0.000 description 1
- XVDRBLNFXJXVQQ-UHFFFAOYSA-N 2,5-dichloro-1,3-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Cl)=CC(C(F)(F)F)=C1Cl XVDRBLNFXJXVQQ-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- VCRGRFBFHUEHFN-UHFFFAOYSA-N 2-chloro-1,3-bis(trichloromethyl)benzene Chemical compound ClC1=C(C(Cl)(Cl)Cl)C=CC=C1C(Cl)(Cl)Cl VCRGRFBFHUEHFN-UHFFFAOYSA-N 0.000 description 1
- QULONSINRUUAHY-UHFFFAOYSA-N 2-chloro-1,3-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C(F)(F)F)=C1Cl QULONSINRUUAHY-UHFFFAOYSA-N 0.000 description 1
- URRUNMMSCQPLOQ-UHFFFAOYSA-N 2-chloro-1,4-bis(trichloromethyl)benzene Chemical compound ClC1=CC(C(Cl)(Cl)Cl)=CC=C1C(Cl)(Cl)Cl URRUNMMSCQPLOQ-UHFFFAOYSA-N 0.000 description 1
- IDNVTCBYGYOPKJ-UHFFFAOYSA-N 2-chloro-1,4-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(C(F)(F)F)C(Cl)=C1 IDNVTCBYGYOPKJ-UHFFFAOYSA-N 0.000 description 1
- ZFFRILSTJJYXJB-UHFFFAOYSA-N 2-chloro-1-(trichloromethyl)-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C(Cl)(Cl)Cl)=C1Cl ZFFRILSTJJYXJB-UHFFFAOYSA-N 0.000 description 1
- PZDYHFIAZBXOSZ-UHFFFAOYSA-N 2-chloro-1-(trichloromethyl)-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(C(Cl)(Cl)Cl)C(Cl)=C1 PZDYHFIAZBXOSZ-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- JDZLOJYSBBLXQD-UHFFFAOYSA-N difluoromethylbenzene Chemical compound FC(F)C1=CC=CC=C1 JDZLOJYSBBLXQD-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- GPGMRSSBVJNWRA-UHFFFAOYSA-N hydrochloride hydrofluoride Chemical compound F.Cl GPGMRSSBVJNWRA-UHFFFAOYSA-N 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2549095A DE2549095C3 (de) | 1975-11-03 | 1975-11-03 | Verfahren zur Herstellung von in den Seitenketten fluorierten und chlorierten Xylolen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5259119A JPS5259119A (en) | 1977-05-16 |
| JPS6126529B2 true JPS6126529B2 (nl) | 1986-06-20 |
Family
ID=5960694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51122993A Granted JPS5259119A (en) | 1975-11-03 | 1976-10-15 | Preparation of trichloromethyll trifluoromethyllbenzene |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4079090A (nl) |
| JP (1) | JPS5259119A (nl) |
| BE (1) | BE847306A (nl) |
| BR (1) | BR7606947A (nl) |
| CH (1) | CH621759A5 (nl) |
| DE (1) | DE2549095C3 (nl) |
| FR (1) | FR2329626A1 (nl) |
| GB (1) | GB1512609A (nl) |
| IT (1) | IT1069072B (nl) |
| NL (1) | NL7611450A (nl) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4183873A (en) * | 1976-11-01 | 1980-01-15 | Hooker Chemicals & Plastics Corp. | Liquid phase fluorination process |
| JPS54130524A (en) * | 1978-03-30 | 1979-10-09 | Daikin Ind Ltd | Preraration of trifluoromethylbenzene or its derivative |
| US4581179A (en) * | 1980-04-16 | 1986-04-08 | Occidental Chemical Corporation | Process for the preparation of trifluoromethylbenzoyl chlorides and bromides from trifluoromethylbenzoyl fluorides |
| US4500471A (en) * | 1980-04-16 | 1985-02-19 | Occidental Chemical Corporation | Preparation of trifluoromethyl-benzoyl halides |
| US4367348A (en) * | 1980-10-10 | 1983-01-04 | Occidental Chemical Corporation | Novel trifluoromethyl benzal chlorides and process for the preparation thereof |
| US4966988A (en) * | 1989-02-17 | 1990-10-30 | Chevron Research Company | Process for preparing acetonitrile 3-trifluoromethyl benzene |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1967244A (en) * | 1932-08-31 | 1934-07-24 | Kinetic Chemicals Inc | Production of organic fluorine compounds |
| US2174512A (en) * | 1933-11-24 | 1939-10-03 | Kinetic Chemicals Inc | Dielectric materials |
| JPS4328086Y1 (nl) * | 1965-02-16 | 1968-11-20 | ||
| US3457310A (en) * | 1967-01-23 | 1969-07-22 | Dow Chemical Co | Hexahaloxylidides |
| GB1416181A (en) * | 1972-01-17 | 1975-12-03 | Secr Defence | Processes for the manufacture of fluoroalkylaromatic compounds |
-
1975
- 1975-11-03 DE DE2549095A patent/DE2549095C3/de not_active Expired
-
1976
- 1976-10-12 US US05/731,478 patent/US4079090A/en not_active Expired - Lifetime
- 1976-10-13 GB GB42547/76A patent/GB1512609A/en not_active Expired
- 1976-10-14 CH CH1305576A patent/CH621759A5/de not_active IP Right Cessation
- 1976-10-15 JP JP51122993A patent/JPS5259119A/ja active Granted
- 1976-10-15 BR BR7606947A patent/BR7606947A/pt unknown
- 1976-10-15 NL NL7611450A patent/NL7611450A/nl not_active Application Discontinuation
- 1976-10-15 BE BE2055378A patent/BE847306A/xx not_active IP Right Cessation
- 1976-10-15 IT IT51756/76A patent/IT1069072B/it active
- 1976-10-15 FR FR7631166A patent/FR2329626A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2549095B2 (de) | 1977-08-25 |
| BE847306A (fr) | 1977-04-15 |
| GB1512609A (en) | 1978-06-01 |
| BR7606947A (pt) | 1977-08-30 |
| IT1069072B (it) | 1985-03-25 |
| DE2549095A1 (de) | 1977-05-05 |
| CH621759A5 (nl) | 1981-02-27 |
| FR2329626A1 (fr) | 1977-05-27 |
| US4079090A (en) | 1978-03-14 |
| DE2549095C3 (de) | 1978-04-20 |
| FR2329626B1 (nl) | 1982-11-12 |
| JPS5259119A (en) | 1977-05-16 |
| NL7611450A (nl) | 1977-05-05 |
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